Oxymorphindole | CAS#111469-88-6 | δ-Opioid receptor agonist

MedKoo Cat#: 466029 | Name: Oxymorphindole

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxymorphindole is a δ-Opioid receptor agonist.

Chemical Structure

Oxymorphindole

CAS#111469-88-6

Theoretical Analysis

MedKoo Cat#: 466029

Name: Oxymorphindole

CAS#: 111469-88-6

Chemical Formula: C23H22N2O3

Exact Mass: 374.1630

Molecular Weight: 374.44

Elemental Analysis: C, 73.78; H, 5.92; N, 7.48; O, 12.82

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Oxymorphindole; OMI;

IUPAC/Chemical Name

(4bS,8R,8aS,14bR)-7-methyl-5,6,7,8,14,14b-hexahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazole-1,8a(9H)-diol

InChi Key

YQNZUKAKYJMEFE-LMDOGRNLSA-N

InChi Code

InChI=1S/C23H22N2O3/c1-25-9-8-22-18-12-6-7-16(26)20(18)28-21(22)19-14(11-23(22,27)17(25)10-12)13-4-2-3-5-15(13)24-19/h2-7,17,21,24,26-27H,8-11H2,1H3/t17-,21+,22+,23-/m1/s1

SMILES Code

O[C@@]1(CC2=C([C@]3([H])O4)NC5=CC=CC=C25)[C@@]63CCN(C)[C@]1([H])CC7=C6C4=C(O)C=C7

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 374.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Griffith JI, Kim M, Bruce DJ, Peterson CD, Kitto KF, Mohammad AS, Rathi S, Fairbanks CA, Wilcox GL, Elmquist WF. Central Nervous System Distribution of an Opioid Agonist Combination with Synergistic Activity. J Pharmacol Exp Ther. 2022 Jan;380(1):34-46. doi: 10.1124/jpet.121.000821. Epub 2021 Oct 18. PMID: 34663676. 2: Uhelski ML, Bruce D, Speltz R, Wilcox GL, Simone DA. Topical Application of Loperamide/Oxymorphindole, Mu and Delta Opioid Receptor Agonists, Reduces Sensitization of C-fiber Nociceptors that Possess NaV1.8. Neuroscience. 2020 Oct 15;446:102-112. doi: 10.1016/j.neuroscience.2020.08.022. Epub 2020 Aug 25. PMID: 32858141; PMCID: PMC7532699. 3: Bruce DJ, Peterson CD, Kitto KF, Akgün E, Lazzaroni S, Portoghese PS, Fairbanks CA, Wilcox GL. Combination of a δ-opioid Receptor Agonist and Loperamide Produces Peripherally-mediated Analgesic Synergy in Mice. Anesthesiology. 2019 Sep;131(3):649-663. doi: 10.1097/ALN.0000000000002840. PMID: 31343460; PMCID: PMC6693899. 4: Schuster DJ, Metcalf MD, Kitto KF, Messing RO, Fairbanks CA, Wilcox GL. Ligand requirements for involvement of PKCε in synergistic analgesic interactions between spinal μ and δ opioid receptors. Br J Pharmacol. 2015 Jan;172(2):642-53. doi: 10.1111/bph.12774. Epub 2014 Nov 24. PMID: 24827408; PMCID: PMC4292975. 5: Bradbury FA, Zelnik JC, Traynor JR. G protein independent phosphorylation and internalization of the delta-opioid receptor. J Neurochem. 2009 Jun;109(5):1526-35. doi: 10.1111/j.1471-4159.2009.06082.x. Epub 2009 Apr 1. PMID: 19344370; PMCID: PMC4372060. 6: Jutkiewicz EM, Baladi MG, Folk JE, Rice KC, Woods JH. The delta-opioid receptor agonist SNC80 [(+)-4-[alpha(R)-alpha-[(2S,5R)-4-allyl-2,5-dimethyl-1-pi perazinyl]-(3-methoxybenzyl)-N,N-diethylbenzamide] synergistically enhances the locomotor-activating effects of some psychomotor stimulants, but not direct dopamine agonists, in rats. J Pharmacol Exp Ther. 2008 Feb;324(2):714-24. doi: 10.1124/jpet.107.123844. Epub 2007 Nov 6. PMID: 17986650. 7: Metcalf MD, Coop A. 5'-halogenated analogs of oxymorphindole. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5916-7. doi: 10.1016/j.bmcl.2007.07.098. Epub 2007 Aug 23. PMID: 17826993; PMCID: PMC2062523. 8: Wu HE, Sun HS, Darpolar M, Dunn W 3rd, Tseng LF. Antinociceptive properties of oxymorphazole in the mouse. Eur J Pharmacol. 2003 Jul 25;473(2-3):143-8. doi: 10.1016/s0014-2999(03)01912-5. PMID: 12892831. 9: Grundt P, Jales AR, Traynor JR, Lewis JW, Husbands SM. 14-amino, 14-alkylamino, and 14-acylamino analogs of oxymorphindole. Differential effects on opioid receptor binding and functional profiles. J Med Chem. 2003 Apr 10;46(8):1563-6. doi: 10.1021/jm021073r. PMID: 12672258. 10: Hosohata Y, Varga EV, Stropova D, Li X, Knapp RJ, Hruby VJ, Rice KC, Nagase H, Roeske WR, Yamamura HI. Mutation W284L of the human delta opioid receptor reveals agonist specific receptor conformations for G protein activation. Life Sci. 2001 Apr 6;68(19-20):2233-42. doi: 10.1016/s0024-3205(01)01011-6. PMID: 11358332. 11: Shenderovich MD, Liao S, Qian X, Hruby VJ. A three-dimensional model of the delta-opioid pharmacophore: comparative molecular modeling of peptide and nonpeptide ligands. Biopolymers. 2000 Jun;53(7):565-80. doi: 10.1002/(SICI)1097-0282(200006)53:7<565::AID-BIP4>3.0.CO;2-5. PMID: 10766952. 12: Coop A, Jacobson AE. The LMC delta opioid recognition pharmacophore: comparison of SNC80 and oxymorphindole. Bioorg Med Chem Lett. 1999 Feb 8;9(3):357-62. doi: 10.1016/s0960-894x(98)00745-8. PMID: 10091684. 13: Clark MJ, Emmerson PJ, Mansour A, Akil H, Woods JH, Portoghese PS, Remmers AE, Medzihradsky F. Opioid efficacy in a C6 glioma cell line stably expressing the delta opioid receptor. J Pharmacol Exp Ther. 1997 Nov;283(2):501-10. PMID: 9353363. 14: Lomize AL, Pogozheva ID, Mosberg HI. Development of a model for the delta- opioid receptor pharmacophore: 3. Comparison of the cyclic tetrapeptide, Tyr-c[D-Cys-Phe-D-Pen]OH with other conformationally constrained delta-receptor selective ligands. Biopolymers. 1996 Feb;38(2):221-34. doi: 10.1002/(SICI)1097-0282(199602)38:2%3C221::AID-BIP8%3E3.0.CO;2-X. PMID: 8589255. 15: Lai J, Ma SW, Zhu RH, Rothman RB, Lentes KU, Porreca F. Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1b subtype. Neuroreport. 1994 Oct 27;5(16):2161-4. doi: 10.1097/00001756-199410270-00043. PMID: 7865767. 16: Xu H, Partilla JS, de Costa BR, Rice KC, Rothman RB. Interaction of opioid peptides and other drugs with multiple delta ncx binding sites in rat brain: further evidence for heterogeneity. Peptides. 1992 Nov-Dec;13(6):1207-13. doi: 10.1016/0196-9781(92)90030-7. PMID: 1337380. 17: Carr DJ, Radulescu RT, DeCosta BR, Rice KC, Blalock JE. Opioid modulation of immunoglobulin production by lymphocytes isolated from Peyer's patches and spleen. Ann N Y Acad Sci. 1992 Apr 15;650:125-7. doi: 10.1111/j.1749-6632.1992.tb49108.x. PMID: 1605469. 18: Takemori AE, Sultana M, Nagase H, Portoghese PS. Agonist and antagonist activities of ligands derived from naltrexone and oxymorphone. Life Sci. 1992;50(20):1491-5. doi: 10.1016/0024-3205(92)90138-f. PMID: 1315896. 19: Remmers AE, Medzihradsky F. Resolution of biphasic binding of the opioid antagonist naltrexone in brain membranes. J Neurochem. 1991 Oct;57(4):1265-9. doi: 10.1111/j.1471-4159.1991.tb08288.x. PMID: 1654389. 20: Jiang Q, Rice KC, deCosta B, Porreca F. Effects of oxymorphindole on morphine induced-antinociception in mice and rats. NIDA Res Monogr. 1990;105:384-5. PMID: 1652080.